Ammonium Chloride → 2-Ethoxy-4-aminobenzoic acid

HRID 2263949

Reaktionsgleichung

Reaktionsgleichung von HRID 2263949
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:13][C:11]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 27363472-Ethoxy-4-nitrobenzoic acid

Produkt 1

HCID 101763852-Ethoxy-4-aminobenzoic acidAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Ethoxy-4-nitrobenzoic acid (20 g, 94 mmol, Aldrich) was suspended in ethanol (170 mL) and combined with a saturated aqueous solution of ammonium chloride (100 mL). As this was rapidly stirred, iron dust (13.3 g, 239 mmol) was added in portions. The temperature was raised to 80° C. for 1 h. The cooled suspension was filtered through Celite, and the cake washed with dichloromethane (150 mL). The filtrate was diluted with dichloromethane and washed with brine, dried over magnesium sulfate, filtered and evaporated. A brown solid was triturated with dichloromethane and filtered to give 15 g of 4-amino-2-ethoxybenzoic acid (88%).

Aufarbeitung

  1. filtrationThe cooled suspension was filtered through Celite
  2. washthe cake washed with dichloromethane (150 mL)
  3. additionThe filtrate was diluted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customA brown solid was triturated with dichloromethane
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-6840192751e7404f86f9691611b22422
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851626B2

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